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Caribbean

Caribbean

Candy-colored cocktails sipped in seaside watering holes. Carefree days followed by calypso-flavored nights. These are the siren songs that lure anyone with a yacht and a yearning to escape to the incomparable Caribbean Islands. Whether you’re sailing through turquoise waters, lazing on powdery white beaches, the glamorous harbors and unknown coves of this area remain a hidden treasure.
 
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4-Day Bahamas & Key West

Starting from $399*

Cruise Line: Holland America Line

Ship: ms Nieuw Statendam

Sailing Dates: Jan 27 2021

Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

( Note: Optional tours are available from most ports for an additional charge. )

7-Day Eastern Caribbean

Starting from $699*

Cruise Line: Holland America Line

Ship: ms Eurodam

Sailing Dates:  Feb 14 2021 | Mar 07 2021 | Mar 28 2021

Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

( Note: Optional tours are available from most ports for an additional charge. )

7-Day Western Caribbean

Starting from $699*

Cruise Line: Holland America Line

Ship: ms Eurodam

Sailing Dates:  Jan 31 2021 | Feb 21 2021 | Mar 14 2021 | Apr 04 2021

Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

( Note: Optional tours are available from most ports for an additional charge. )

7-Day Western Caribbean

Starting from $749*

Cruise Line: Holland America Line

Ship: ms Nieuw Amsterdam

Sailing Dates:  Jan 23 2021 | Feb 13 2021 | Apr 07 2021

Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

( Note: Optional tours are available from most ports for an additional charge. )

7-Day Tropical Caribbean

Starting from $749*

Cruise Line: Holland America Line

Ship: ms Eurodam

Sailing Dates:  Feb 07 2021 | Feb 28 2021 | Mar 21 2021

Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

( Note: Optional tours are available from most ports for an additional charge. )

7-Day Eastern Caribbean

Starting from $649*

Cruise Line: Holland America Line

Ship: ms Nieuw Amsterdam

Sailing Dates:  Feb 06 2021 | Feb 27 2021

Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

( Note: Optional tours are available from most ports for an additional charge. )

7 days - Classic Caribbean [St. Maarten to St. Maarten]

Starting from $1,299*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates:  Feb 13 2021 | Apr 03 2021 | Dec 11 2021 | Mar 05 2022 | Mar 19 2022

Port: St. Maarten to St. Maarten

( Note: Optional tours are available from most ports for an additional charge. )

7 days - Yachtsman's Caribbean [St. Maarten to St. Maarten]

Starting from $1,499*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates:  Feb 06 2021 | Mar 27 2021 | Jan 08 2022 | Mar 12 2022 | Mar 26 2022

Port: St. Maarten to St. Maarten

( Note: Optional tours are available from most ports for an additional charge. )

7 days - Windward Islands Surf & Sunsets [San Juan to San Juan]

Starting from $1,399*

Cruise Line: Windstar Cruise

Ship: Star Breeze / Star Pride

Sailing Dates:  Jan 30 2021 | Feb 27 2021 | Mar 13 2021 | Mar 27 2021 | NOV 20 2021 | Dec 04 2021 | Jan 15 2022 | Jan 29 2022 | Feb 12 2022 | Feb 26 2022 | Mar 12 2022

Port: San Juan to San Juan

( Note: Optional tours are available from most ports for an additional charge. )

7 days - San Juan & the Virgin Islands [San Juan to San Juan]

Starting from $1,399*

Cruise Line: Windstar Cruise

Ship: Star Breeze / Star Pride

Sailing Dates:  Jan 23 2021 | Feb 06 2021 | Mar 06 2021 | Mar 20 2021 | Nov 13 2021 | Nov 27 2021 | Dec 11 2021 | Jan 08 2022 | Feb 05 2022 | Feb 19 2022

Port: San Juan to San Juan

( Note: Optional tours are available from most ports for an additional charge. )

7 days - Lush & Lovely Islands of the Lesser Antilles [St. Maarten to Bridgetown]

Starting from $1,399*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates:  Feb 20 2021 | Jan 15 2022

Port: St. Maarten to Bridgetown

( Note: Optional tours are available from most ports for an additional charge. )

7-Day Tropical Caribbean

Starting from $699*

Cruise Line: Holland America Line

Ship: ms Nieuw Amsterdam

Sailing Dates:  Mar 13 2021

Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

( Note: Optional tours are available from most ports for an additional charge. )

7 days - Jewels of the Windward Islands [Bridgetown to Bridgetown]

Starting from $1,499*

Cruise Line: Windstar Cruise

Ship: Wind Surf / Wind Star

Sailing Dates:  Jan 23 2021 | Feb 27 2021 | Mar 13 2021 | Jan 22 2022 | Feb 26 2022 | Mar 05 2022 | Mar 12 2022

Port: Bridgetown to Bridgetown

( Note: Optional tours are available from most ports for an additional charge. )

7 days - Uncovering the Windward Wonders of the Caribbean [Bridgetown to Bridgetown]

Starting from $1,399*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates:  Mar 06 2021

Port: Bridgetown to Bridgetown

( Note: Optional tours are available from most ports for an additional charge. )

7-Day Tropical Caribbean

Starting from $799*

Cruise Line: Holland America Line

Ship: ms Nieuw Amsterdam

Sailing Dates: Jan 30 2021

Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

( Note: Optional tours are available from most ports for an additional charge. )

7 days - Lush & Lovely Islands of the Lesser Antilles [Bridgetown to St. Maarten]

Starting from $1,399*

Cruise Line: Windstar Cruise

Ship: Wind Surf / Wind Star

Sailing Dates: Jan 30 2021 | Mar 20 2021 | Mar 19 2022

Port: Bridgetown to St. Maarten

( Note: Optional tours are available from most ports for an additional charge. )

7-Day Eastern Caribbean

Starting from $699*

Cruise Line: Holland America Line

Ship: ms Nieuw Amsterdam

Sailing Dates: Mar 31 2021

Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

( Note: Optional tours are available from most ports for an additional charge. )

7 Days - Windward Ways & Tobago Cays [Bridgetown to Oranjestad]

Starting from $2,499*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: Jan 29 2022

Port: Bridgetown to Oranjestad

( Note: Optional tours are available from most ports for an additional charge. )

9 Days - The Allure of the Antilles [San Juan to Miami]

Starting from $1,499*

Cruise Line: Windstar Cruise

Ship: Star Breeze

Sailing Dates: Apr 03 2021

Port: San Juan to Miami

( Note: Optional tours are available from most ports for an additional charge. )

9 Days - In the Wake of the Spanish Armadas [Oranjestad to Colón]

Starting from $2,199*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: Feb 05 2022

Port: Oranjestad to Colón

( Note: Optional tours are available from most ports for an additional charge. )

*Prices are per person, based on double occupancy. Prices do not include Government Fees & Taxes. Pricing and availability subject to change without notice. Cruise Booking reserves the right to refuse or honor any prices / sailings that are erroneously printed or quoted. Terms & Conditions apply.